The art of listening

Chase Butler
Aug 22, 2017 · 6 min read

By: Chase Butler (chasebutlerblog.com)

I know someone who says “mother fell in a well” when people ask how he is doing to see if the person is actually listening. I’ve witnessed a server politely respond to him with “that’s wonderful!” in the sweetest tone and with no awareness of his mother’s fictional misfortune. We exploded in laughter, and I can’t say the server was as thrilled as we were when we explained.

Years later now, I look back on that story as a reminder that listening well for most of us doesn’t come naturally. It normally requires a concerted effort over a long period of time before we become great listeners. History’s great thinkers and writers have had plenty to say on the subject:

“Most people do not listen with the intent to understand; they listen with the intent to reply.” (Stephen Covey)

“Seek first to understand, then to be understood.” (Stephen Covey)

“If one gives an answer before he hears, it is his folly and shame.” (Proverbs 18:13)

“Let every person be quick to hear, slow to speak, slow to anger.” (James 1:19)

“When people talk, listen completely. Most people never listen.” (Ernest Hemingway)

I’ve found the quickest way to fast-track progress in any context, particularly relationships, is not a formula broken down into ten easy-to-follow steps. Rather, it’s simply learning to listen well and ask great questions.

Over the last few months I’ve been compiling a list of questions. When the setting has been appropriate I’ve asked a few people I know to answer them. I always prefaced it with “let me know if this gets boring.” No one has turned me down yet, and it’s seemed everyone has genuinely enjoyed getting to talk about themselves.

So today I’m going to answer a few of my favorite questions from the list and leave you with the rest. My hope is that you’ll not only have some ammo for asking great questions, but that it will provide a setting for you to listen well. Plus, it’s just fun. Among four of us, we didn’t stop talking for an entire five-hour car ride home.

What is the first memory in your brain?

I would have been around two or three years old. We lived in an apartment in Huntsville. In the afternoon I would sit at the counter outside of the kitchen and eat a dill pickle. When my Dad would get home he would walk up from behind and kiss me on the back of my neck. I vividly recall how prickly his mustache was.

If I were to give you $10,000 right now, what would you do (can’t pay bills or debts)?

Go eat hibachi for dinner. Take off work the next day. Go buy a 2000 Toyota 4Runner, trailer, and dirt bike. Spend the weekend riding in the woods.

You have to get a tattoo today. What’s it going to be?

“I believe, help my unbelief.”

What is the one outfit you would wear every day for the rest of your life?

Boots, jeans, gray t-shirt.

What celebrity would you most prefer to look like?

Hugh Jackman (when I’m 40).

Describe your parents’ personalities in a few words.

Mom: kind, compassionate, communicator. Dad: hardworking, consistent, determined.


The List

  • If I were to ask your parents what you were known for as a child, what would they tell me?
  • What is your dream job (money is no object and you can snap your fingers and have the education needed)?
  • Describe your perfect day off of work.
  • When do you feel the loneliest?
  • Money is no object, what are you doing tomorrow?
  • No consequences (jail time or permanent damage), who would you punch in the face right now?
  • What is your favorite quote or mantra?
  • If you could take any vacation, where would you go?
  • Money is no object, what cause are you contributing towards? (example: world hunger, orphans, clean drinking water)
  • When do you feel the most insecure?
  • What is your strangest fear or phobia?
  • What is the first memory in your brain?
  • What book has shaped you as a person more than any other?
  • Who is your hero?
  • Would you prefer to live in ignorant bliss or painful reality?
  • Who would you die for without hesitation?
  • What moment in your life would you relive (not redo, just experience again)?
  • What is your worst habit?
  • What movie has made you cry (for the non-criers, favorite movie)?
  • What is the biggest offense you’ve ever forgiven?
  • What do you regret?
  • What is the worst purchase you’ve ever made? Best? Best under $10?
  • What is the biggest privilege or opportunity you’ve been given that you didn’t earn?
  • What would you tell your 18 year-old self?
  • Who was your first best friend?
  • What’s the worst job you’ve ever had?
  • What’s the biggest sacrifice you’ve made for someone else?
  • What’s the biggest sacrifice someone has made for you?
  • What is your favorite memory from college (or just age 18–22)?
  • Who was your worst boyfriend or girlfriend?
  • Describe your dream house.
  • What do you need right now more than anything?
  • What do you want more than anything right now?
  • What is your love language (quality time, physical touch, words of affirmation, gifts, acts of service)?
  • On a scale of 1–10, how happy are you right now?
  • On a scale of 1–10, how fulfilled are you right now?
  • What is your favorite personality trait about yourself.
  • Who have you hurt in your life?
  • Favorite TV show of all time?
  • What is your biggest temptation?
  • It’s after midnight and we’re hungry, where are we going to eat?
  • Have you ever experience something supernatural?
  • Describe your most relaxing scenario.
  • What celebrity would you most prefer to look like?
  • What’s the best advice you’ve ever been given? Worst?
  • What have you changed your mind about?
  • What’s your favorite food of all time?
  • What was the hardest year of your childhood?
  • Describe your parents’ personalities in a few words.
  • You have to get a tattoo today. What’s it going to be?
  • You can choose how you die. How is it happening?
  • What is the worst physical pain you’ve ever felt?
  • What is the one outfit you would wear every day for the rest of your life?
  • Your friends describe you in one word. What is it?
  • What setting or context do you most frequently find inspiration or have great ideas?
  • What is your most deeply held belief?
  • If you could put anything on a billboard, what would it be?
  • What did you love to do as a child that you no longer do?
  • For many people there is a day when everything changes, when you world is turned upside down, when a huge shift in your existence occurs. Have you had that moment?
  • If you started college over, would you have chosen a different path?
  • What’s been the best part of today? Worst?
  • What is something you do that is probably a pet peeve to someone else?
  • What makes you happier than anything else?
  • Dinner is on me. Where are we going?
  • When do you feel the least loved?
  • What’s the biggest challenge you’re facing right now?
  • What’s the biggest challenge you’ve overcome in the past?
  • Describe a failure of yours and what you learned.
  • What part of relationships scares you the most?
  • What’s your best habit?
  • What’s the best investment of time and money you’ve ever made?
  • What is something you believe that others might think is absurd?
  • If I were to give you $10,000 right now, what would you do (can’t pay bills or debts)?
  • Do you believe in ghosts? Aliens?
  • What’s your favorite meal under $10?
  • What’s your biggest slob tendency?
  • What’s the worst action you’ve contemplated doing but didn’t do?
  • How do you unwind or escape daily?
  • You can only drink one drink the rest of your life. What is it?
  • You can create a rule everyone in the world has to follow. What would it be?

Read more posts at chasebutlerblog.com

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Chase Butler

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🖊chasebutlerblog.com / 📩 chasebutlerblog@gmail.com / 🏡Birmingham, AL

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